Gambler by samwisethedm (2024)

A tiefling, tumbling the dice between his fingers, looks across the table in the smoke-filled tavern at his self-assured opponent. His eyes flick to the mound of gold and silver in the center of the table. His opponent is sure he's won all that coin. But when the dice clatter across the table, bouncing this way and that, clattering off goblets, they all land impossibly perfectly. The tiefling is the victor.

Gambler
LevelProficiency BonusFeaturesLuck Modifier
1st+2Gambler's Attack, Luck, Well of Fortune (two uses)+1
2nd+2Pit of Misfortune, Place Your Bets+1
3rd+2Gambling Specialty+1
4th+2Ability Score Improvement, All or Nothing+1
5th+3New Gambler's Attack+2
6th+3Gambler's Attack improvement, Well of Fortune (four uses)+2
7th+3Gambling Specialty feature+2
8th+3Ability Score Improvement+2
9th+4New Gambler's Attack+3
10th+4Dice with Death, Gambling Specialty feature+3
11th+4Gambler's Attack improvement, Well of Fortune (six uses)+3
12th+4Ability Score Improvement, All or Nothing improvement+3
13th+5New Gambler's Attack+4
14th+5Gambling Specialty feature+4
15th+5Pit of Misfortune improvement+4
16th+5Ability Score Improvement, Gambler's Attack improvement+4
17th+6Vices, Well of Fortune (eight uses)+5
18th+6Gambling Specialty feature, New Gambler's Attack+5
19th+6Ability Score Improvement, All or Nothing improvement+5
20th+6A Fighting Chance+5

 A halfling steps up to the gallows, arms tied behind her back. The executioner has to fetch a ladder in order for her tobe able to reach the noose. As the rope slips around her neckand the crowd boos, she exhales softly, then glances upward. The knot is fraying. She smiles. She's not out of luck just yet.

A wood elf and her dwarven companion, outnumbered five to two, desperately fend off their attackers. After an exceptional dodge, the wood elf brings her scimitar around toward the face of one of her foes. As it moves through the air, lightning surges to life on its blade, crackling in the reflection in her foe's now-terrified eyes. The tables have turned.

While gamblers rely on their skill, deftness, and charm to survive high-stakes adventures, their most precious resource is luck. Gambling with the very powers that bind the universe, they have an uncanny knack for succeeding when they should not. They're not simply hobby or compulsive gamblers (though they may be), but rather, extraordinary individuals who have been able to tap into the forces of chance and probability since birth.

Everything to Chance

Many adventurers pride themselves on leaving nothing to chance by excelling at what they do, but gamblers have the foresight to recognize that the opposite is ultimately true, no matter how prepared they are. Therefore, they dedicate their skills and knowledge toward not only accomplishing their goals, but responding to the unexpected ways in which those goals can unfold.

Molding Fortunes

Gamblers may be in it for the money, as is the connotation of their namesake, but what they are truly in it for is to shape their future. Having tapped into the cosmic energies of both fortune and misfortune, they are able to bend fate to their will, but not without taking risks.

Creating a Gambler

When creating a gambler, consider your character's goals. Are they hoping to get rich? Working to pay off debts incurred by their addictions? Or perhaps it's something more noble, like trying to protect the less fortunate, or rescuing their child? You should also consider how their skills and luck affect their personality. Does it make them reckless or impulsive? Contrarily, perhaps it makes them cautious and fearful. Or maybe they've just lost it and are along for the ride. There are many reasons to become a gambler and many ways in which it can impact someone.

Quick Build

You can make a gambler quickly by following these suggestions. First, Dexterity should be your highest ability score. Make either Intelligence, Wisdom, or Charisma your next highest ability score, depending on if you want to emphasize logic, street smarts, or charm. Second, choose either the Charlatan or Entertainer background.

Class Features

As a gambler, you gain the following class features.

Hit Points

  • Hit Dice: 1d8 per gambler level
  • Hit Points at 1st Level: 8 + your Constitution modifier
  • Hit Points at Higher Levels: 1d8 + your Constitution modifier for every gambler level after 1st

Proficiencies

  • Armor: Light armor
  • Weapons: Simple weapons, blowguns, hand crossbows, nets, rapiers, scimitars, whips
  • Tools: 3 gaming sets of your choice
  • Saving Throws: Wisdom, Charisma
  • Skills: Choose four from Acrobatics, Animal Handling, Arcana, Deception, History, Insight, Intimidation, Investigation, Perception, Performance, Persuasion, Sleight of Hand, Stealth, and Survival

Equipment

You start with the following equipment, in addition to the equipment granted by your background:

  • (a) a rapier or (b) a scimitar
  • (a) a light crossbow and 20 bolts or (b) 50 darts
  • (a) an entertainer's pack, (b) a burglar's pack, or (c) a diplomat's pack
  • Two gaming sets of your choice
  • Leather armor and a dagger

Gambler's Attack

At 1st level, you learn one gambler's attack of your choice from the list in the Gambler's Attacks subsection. You may use this feature as an action once per combat to imbue an attack with additional power.

You learn additional gambler's attacks at 5th, 9th, 13th, and 18th levels, and you may use each once per combat.

Your gambler's attacks improve at 6th, 11th, and 16th levels as detailed in their own description.

Luck

As a gambler, Luck is something you constantly have to contend with, but it is also a resource that you grow over time. As such, beginning at 1st level, you have a Luck modifier, which factors into some features detailed later. Your Luck modifier starts at +1, and increases as shown in the Luck Modifier column of the Gambler table.

Well of Fortune

Starting at 1st level, you have a limited well of fortune you may draw upon at any time. Before making an attack roll, ability check, or saving throw, you may use this feature to roll with advantage. Alternatively, you may use this to remove disadvantage imposed on you for one of the aforementioned rolls. You may use this feature twice per long rest.

You gain two additional uses at 6th, 11th, and 17th levels.

Pit of Misfortune

Starting at 2nd level, you may use this feature once per long

rest to automatically succeed on any ability check, saving throw, or attack roll. However, once you have done this, misfortune will befall you at some time in the future. At any point between now and your next long rest, any two of your successful rolls will be turned into a failure. Your DM determines which rolls these will be.

Starting at 15th level, only one of your subsequent successes will be turned into a failure , and the feature nowresets after either a short or long rest.

Place Your Bets

Starting at 2nd level, once per long rest, you have advantage on Charisma checks to convince someone to bet something you desire against you, provided you bet something equally valuable in return. If you succeed in convincing them, the contest to determine the outcome of the bet should be proposed by you and worked out between you and the chosen NPC, and you may add your Luck modifier to all requisite rolls for said contest.

Gambling Specialty

At 3rd level you choose a gambling specialty. This grants you features when you choose it, and again at 7th, 10th, 14th, and 18th levels. You can find details in the Gambling Specialties subsection.

Ability Score Improvement

When you reach 4th level, and again at 8th, 12th, 16th, and 19th level, you can increase one ability score of your choice by 2, or you can increase two ability scores of your choice by 1. As normal, you can’t increase an ability score above 20 using this feature.

All or Nothing

Starting at 4th level, you roll a critical success with a 19 or 20, but you roll a critical failure with a 1 or 2. Starting at 12th level, rolling an 18 is also a critical success, but a 3 is also a critical failure. Starting at 19th level, rolling a 17 is also a critical success, but a 4 is also a critical failure.

Dice with Death

Starting at 10th level, any time you have to make a death saving throw, before making a roll, you may use this feature to count all subsequent rolls as critical failures or critical successes. Therefore, 1-10 is a critical failure, and 11-20 is a critical success. A critical failure counts as two failed rolls, and a critical success counts as two successful rolls. This feature wears off once you have become stable, or conversely, died. You may use this feature after you have already started making death saves, but you can only implement it prior to rolling on your turn.

Vices

At 17th level, choose three vices - one damage type and two conditions. You develop resistance to the damage type and have advantage on saving throws against the conditions. Your damage type options are: acid, bludgeoning, cold, fire, force, lightning, necrotic, piercing, poison, psychic, radiant, slashing, and thunder. Your condition options are: blinded, charmed, deafened, exhaustion, frightened, grappled,

incapacitated, paralyzed, petrified, poisoned, prone, restrained, stunned, and unconscious.

A Fighting Chance

Starting at 20th level, you choose one roll type to which you can add your Luck modifier. You can thenceforth add your Luck modifier to all rolls of this type. You may choose either attack rolls, ability checks, or saving throws.

Gambler's Attacks

When choosing a gambler's attack, you choose from the following list.

Ability Score Gamble

When making an attack roll, you may use this feature to also inflict damage on a target's ability score, resulting in the designated score being lowered by 2. The target's ability score returns to normal after it finishes a long rest. Roll a d6 to determine which ability score is affected.

d6Ability Score
1Strength
2Dexterity
3Constitution
4Intelligence
5Wisdom
6Charisma

Starting at 6th level, you may re-roll the result, though you must stick with the new roll. Starting at 11th level, you roll twice and target two ability scores (or one that decreases by 4 if you roll the same one twice). You may only re-roll one of these. Starting at 16th level, each ability score decreases by 3.

Bonus Action Gamble

When making an attack roll, you may use this feature to grant yourself a bonus action following the attack. Roll a d8 to determine which bonus action you may take.

d8Bonus Action
1Dash
2Disengage
3Dodge
4Extra Attack
5Help Ally
6Hide
7Ready
8Use Item

Starting at 6th level, you may re-roll the result, though you must stick with the new roll. Starting at 11th level, you roll twice and take two bonus actions. You may only re-roll one of them. Starting at 16th level, you roll three times and take the third bonus action on your next turn. You may only re-roll one of these.

Condition Gamble

When making an attack roll, you may use this feature to also inflict a condition on the target. The target must make a Constitution saving throw (Save DC = 8 + your Luck modifier + your proficiency bonus), or be inflicted with this condition for 1 minute. The target may repeat the saving throw at the end of each of its turns. There is, however, always the risk that the condition may work against you.

d12Condition
1Blinded
2Charmed
3Deafened
4Frightened
5Incapacitated
6Invisible
7Paralyzed
8Petrified
9Poisoned
10Prone
11Stunned
12Levels 1-3 Exhaustion

Starting at 6th level, you may re-roll the result, though you must stick with the second result. Starting at 11th level, you roll twice and inflict two conditions. If you roll a duplicate, the duration simply doubles. You may only re-roll one of the two conditions. Starting at 16th level, you roll three times and inflict three conditions. If you roll three duplicates, the duration triples. You may only re-roll two of the three results.

Element Gamble

When making an attack roll, you may use this feature to add 2d6 elemental damage to your attack. Roll a 1d10 to determine which element is added.

d10Element
1Acid
2Cold
3Fire
4Force
5Lightning
6Necrotic
7Poison
8Psychic
9Radiant
10Thunder

The elemental damage increases to 4d6 at 6th level, 6d6 at 11th level, and 8d6 at 16th level. Alternatively, you may roll twice at 6th level for 2d6 per element, two or three times at 11th level for 3d6 or 2d6 per element, and two or four times at 16th level for 4d6 or 2d6 per element.

Loot Gamble

When making an attack roll, you may use this feature to mark a target for loot. If you deliver the killing or otherwise incapacitating blow to the target, you receive special loot from them in addition to any already planned loot. Roll a d6 to determine what kind of loot you receive. The loot must be uncommon or better, but is determined by your DM.

d6Loot
1Armor
2Coins
3Magic Item
4Potion
5Treasure
6Weapon

Starting at 6th level, the rarity increases to rare or better. Starting at 11th level, roll twice to earn additional loot. Starting at 16th level, you receive the special loot regardless of who dealt the final blow.

Planar Gamble

When making an attack roll, you may use this feature to temporarily transport the target to a different plane of existence. The target must make a Dexterity saving throw (Save DC = 8 + your Luck modifier + your proficiency bonus) or be transported to the designated plane for 1 minute, after which they will be returned to the spot they left, alive or dead. Roll a d12 to determine which plane the target is transported to. If you are on one of the following planes, swap it on the chart for the Material Plane.

d12Plane
1Abyss
2Air
3Astral
4Beastlands
5Earth
6Elysium
7Ethereal
8Feywild
9Fire
10Nine Hells
11Shadowfell
12Water

Starting at 6th level, you may re-roll the result, though you must stick with the new roll. Starting at 11th level, the target has disadvantage on the saving throw. Starting at 16th level, the duration increases to 1 hour.

Polymorph Gamble

When making an attack roll, you may use this feature to magically polymorph a target into a weak beast after damage

is dealt. The target must make a Wisdom saving throw (Save DC = 8 + your Luck modifier + your proficiency bonus) or be polymorphed for 1 minute. Roll a d20 to determine which beast they are polymorphed into.

d20Beast
1Baboon
2Badger
3Bat
4Cat
5Crab
6Deer
7Eagle
8Frog
9Giant Fly
10Goat
11Hawk
12Lizard
13Octopus
14Owl
15Rabbit
16Rat
17Raven
18Sea Horse
19Vulture
20Weasel

Starting at 6th level, you may re-roll the resulting beast, though you must stick with the new roll. Starting at 11th level, the target has disadvantage on the saving throw. Starting at 16th level, the duration increases to 1 hour.

Reduction Gamble

When making an attack roll, you may use this feature to reduce the target's statistics. They suffer a reduction as designated on the table, which lasts for 24 hours. Roll a d4 to determine what reduction they receive. The reduction is half the damage dealt to the target.

d4Reduction
1Armor Class
2Damage Dealt
3Hit Point Maximum
4Movement Speed

Starting at 6th level, you may re-roll the resulting reduction, though you must stick with the new roll. Starting at 11th level, the reduction is the full damage rather than half of it. Starting at 16th level, you roll twice and inflict two reductions (or double the reduction in the case of a duplicate roll). You may only re-roll one of these.

Siphon Gamble

When making an attack roll, you may use this feature to siphon health from your enemy. The amount of health you siphon is based on the damage your attack dealt and determined by a d4, and you are healed for the resulting amount.

d4Health Amount
11/4 Damage
21/2 Damage
33/4 Damage
4All Damage

At 6th level, and again at 11th and 16th levels, each die roll's amount increases by 1/4.

Spell Gamble

When making an attack roll, you may use this feature to innately cast a spell as a bonus action following the attack, requiring no material components (your spellcasting ability for this is Luck). You may cast any spell of 1st level or lower

from any spell list from one of the schools of magic, as determined by a d8.

d8School of Magic
1Abjuration
2Conjuration
3Divination
4Enchantment
5Evocation
6Illusion
7Necromancy
8Transmutation

At 6th level the max spell level increases to 2nd. At 11th level it increases to 3rd. At 16th level it increases to 4th.

Terrain Gamble

When making an attack roll, you may use this feature to alter the terrain in a 20 ft. radius centered on your target. The target and any other unwarned creatures in the radius must make a Dexterity saving throw (Save DC = 8 + your Luck modifier + your profiiency bonus) or have disadvantage on any rolls they make on their next turn. When necessary, a terrain is magically sustained even if it is otherwise physically impossible. Roll a d10 to determine what type of terrain this changes to. If it is the same type as the current terrain, you may re-roll until it is a different type.

d10Terrain
1Arctic
2Coastal
3Desert
4Forest
5Grassland
d10Terrain
6Mountain
7Swamp
8Underdark
9Underwater
10Urban

Starting at 6th level, the target has disadvantage on saving throws and ability checks in the resulting terrain. Starting at 11th level, the terrain becomes difficult terrain in a 10-foot radius around the target, and the overall radius increases to 30 ft. Starting at 16th level, the target has disadvantage on attack rolls in the resulting terrain.

Vulnerability Gamble

When making an attack roll, you may use this feature to inflict vulnerability to multiple damage types on the target. They become vulnerable to those damage types for 24 hours. Draw two cards to determine what vulnerabilities they receive. If they are resistant to a resulting damage type, they lose the resistance. If they are immune, the immunity is downgraded to resistance. If they were already vulnerable to the damage type, re-draw. Re-draw if you draw any duplicates, unless it is something that they have resistance or immunity to, as duplicates in that case will further downgrade the effect.

CardVulnerability
AceAcid
2Bludgeoning
3Cold
4Fire
5Force
6Lightning
7Necrotic
8Piercing
9Poison
10Psychic
JackRadiant
QueenSlashing
KingThunder
JokerMagical

Starting at 6th level, you draw 3 cards. Starting at 11th level, you draw 4 cards. Starting at 16th level, you draw 5 cards. The re-drawing rules from above still apply.

Gambling Specialties

Having had enough experience to specialize and hone your skills, you choose one of the following gambling specialties at 3rd level.

Intuition

Those who specialize in Intuition favor reading and charming

people over other considerations. A game's rules or a combat's challenges are not as important as the players involved and how to influence them.

Empathetic Expertise

When you choose this specialty at 3rd level, you gain expertise in one of the following skills in which you are proficient: Animal Handling, Deception, Insight, or Persuasion.

You gain expertise in another one of these skills at 10th level.

Conscious Combatant

Starting at 3rd level when you choose this specialty, having learned to quickly read tells even in combat, you may use your reaction to impose disadvantage on any attack rolls against you if the creature moves at least 5 feet or takes any other actions before attacking.

Talk the Talk

At 7th level, you learn two additional languages of your choice.

Heart and Mind

Starting at 14th level, you may use this feature once per long rest. After making a successful Insight check, you may use this feature to learn exactly what you need to do to get what you want from someone. This can be anything as simple as knowing a bribe of 10 gold will get a guard to let you go or anything as complicated as knowing that if you help find medical treatment for a woman's husband she will smith you a special weapon needed to slay a monster.

Magnetic Charisma

Starting at 18th level, if you are within sight of the roll's target, you may add your Luck modifier to any Charisma check or saving throw made by one of your allies.

Numbers

Those who specialize in Numbers favor counting resources and factoring probabilities over other considerations. The people involved or the skills required are not as important as understanding the system and how to beat it.

Logical Expertise

When you choose this specialty at 3rd level, you gain expertise in one of the following skills in which you are proficient: Arcana, History, Investigation, or Perception.

You gain expertise in another one of these skills at 10th level.

Calculated Combatant

Starting at 3rd level when you choose this specialty, having honed your tactical and analytical skills with mathematical precision, you have advantage on any rolls you have to make during the second round of combat, and any round that begins after the number of combatants has changed (e.g. a creature has died or fled).

Knowledge is Power

At 7th level you become proficient in Intelligence saving throws and you have advantage on Wisdom saving throws when you are at full hit points.

Strategist

Starting at 14th level, you may use this feature twice per long rest. As a reaction, after an ally has made an ability check, attack roll, or saving throw, you may use this feature to call out strategy tips to them, adding your Luck modifier to their roll total. You regain any expended uses after finishing a long rest.

On Top of the Game

Starting at 18th level, you have advantage on Initiative rolls.

Technique

Those who specialize in Technique favor their own practiced capabilities and practical understanding over other considerations. The odds or the people against you are not as important as the competence that you bring to the table.

Technical Expertise

When you choose this specialty at 3rd level, you gain expertise in one of the following skills in which you are proficient: Performance, Sleight of Hand, Stealth, and Survival.

You gain expertise in another one of these skills at 10th level.

Qualified Combatant

At 3rd level when you choose this specialty, having prized technique and skill in turning the tide of combat, you become proficient with martial weapons.

Right Tool for the Job

At 7th level, you become proficient in two additional tools of your choice.

Magician Fingers

Starting at 14th level, you may use this feature twice per long rest to gain advantage on a Sleight of Hand or Performance check you have to make.

Critical Critique

Starting at 18th level, you take 3/4 damage from critical hits, and you may add your Luck modifier to your next roll against the creature that dealt the critical hit to you.

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Gambler by samwisethedm (2024)
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